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WO2004111170A1 - Compositions detergentes liquides aqueuses comprenant des esters anioniques d'alkylpolyglycosides et des enzymes - Google Patents

Compositions detergentes liquides aqueuses comprenant des esters anioniques d'alkylpolyglycosides et des enzymes Download PDF

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Publication number
WO2004111170A1
WO2004111170A1 PCT/EP2004/050966 EP2004050966W WO2004111170A1 WO 2004111170 A1 WO2004111170 A1 WO 2004111170A1 EP 2004050966 W EP2004050966 W EP 2004050966W WO 2004111170 A1 WO2004111170 A1 WO 2004111170A1
Authority
WO
WIPO (PCT)
Prior art keywords
aqueous liquid
liquid detergent
general formula
detergent compositions
anionic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2004/050966
Other languages
English (en)
Inventor
Dario Fornara
Tamara Verzotti
Tullio Pellizzon
Piera Pericu
Yves Galante
Giuseppe Li Bassi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lamberti SpA
Original Assignee
Lamberti SpA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lamberti SpA filed Critical Lamberti SpA
Priority to CA002525211A priority Critical patent/CA2525211A1/fr
Priority to US10/560,145 priority patent/US20070032395A1/en
Priority to EP04741682A priority patent/EP1633841A1/fr
Publication of WO2004111170A1 publication Critical patent/WO2004111170A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/08—Polycarboxylic acids containing no nitrogen or sulfur
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/37—Mixtures of compounds all of which are anionic
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/38—Products with no well-defined composition, e.g. natural products
    • C11D3/386—Preparations containing enzymes, e.g. protease or amylase
    • C11D3/38618—Protease or amylase in liquid compositions only
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/38—Products with no well-defined composition, e.g. natural products
    • C11D3/386—Preparations containing enzymes, e.g. protease or amylase
    • C11D3/38627—Preparations containing enzymes, e.g. protease or amylase containing lipase
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/38—Products with no well-defined composition, e.g. natural products
    • C11D3/386—Preparations containing enzymes, e.g. protease or amylase
    • C11D3/38645—Preparations containing enzymes, e.g. protease or amylase containing cellulase
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/38—Products with no well-defined composition, e.g. natural products
    • C11D3/386—Preparations containing enzymes, e.g. protease or amylase
    • C11D3/38663—Stabilised liquid enzyme compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146—Sulfuric acid esters
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers

Definitions

  • Aqueous liquid detergent compositions comprising anionic esters of alkylpolyglycosides and enzymes.
  • This invention is related to aqueous liquid detergent compositions comprising anionic esters of alkylpolyglycosides and enzymes, and to the procedure for their preparation.
  • the aqueous liquid detergent compositions of the invention exhibit long term enzymatic stability and excellent washing performance.
  • Background Art [0003] It is well known that washing performance of detergents is mainly due to their surfactant composition.
  • such surfactant composition is made of mixtures of anionic, non-ionic, and, in some case, of amphoteric surfactants.
  • the best washing performance is usually obtained by using a combination of anionic and non-ionic surfactants.
  • Another possibility is to improve the stability of enzymes in aqueous detergent compositions by modifying the surfactant compositions.
  • anionic surfactants which, when incorporated in aqueous liquid detergents, could exhibit little inactivating effect on enzymes, or at least surfactants which exhibit a inactivating effect smaller then the one of traditional anionic surfactants.
  • anionic surfactants that, when incorporated in aqueous liquid detergents, can contribute to the washing performance of said mixtures at least as much as the traditional anionic surfactants.
  • anionic esters of alkylpolyglycosides exhibit a low inactivating effect on enzymes, in comparison with the normally used anionic surfactants.
  • anionic esters of alkylpolyglycosides which are described for example in EP 510,564 and in EP 510,565, show in aqueous liquid detergent compositions, comprising them together with an enzyme, a better stability and washing performance then the traditional anionic surfactants.
  • an aqueous liquid detergent composition showing high enzymatic stability and washing performance and comprising: [0020] a.
  • R is an aliphatic group, saturated or unsaturated, linear or branched, having from 6 to 20 atoms of carbon, preferably from 8 to 16 atoms of carbon;
  • G is a residue of a reducing saccharide, preferably of glucose, connected to R-O by means of an ethereal O-glycosidic bond; [0024] O is an oxygen atom;
  • D is an acyl residue of sulfosuccinic acid or of a carboxylic acid selected from the group consisting of citric, tartaric, maleic and malic acid, connected to an oxygen atom of G;
  • n is a number between 1 and m-1 , where m is the number of carboxylic groups in the acid that originates D;
  • x is a number from 1 to 10, representing the average degree of oligomerization of G;
  • y is a number from 1 to 10 representing the degree of average esterificatio ⁇ of (G) x .
  • b from 0.05 to 10 wt%, preferably from 0.10 to 5 wt%, of an enzyme selected in the group consisting of proteases, amylases, lipases, cellulases and mixture thereof;
  • alkylpolyglycosides useful for the realisation of the present invention are: alkylpolyglucoside citrate disodium salt, alkylpolyglucoside sulfosuccinate disodium salt and alkylpolyglucoside tartrate sodium salt, which are respectively available on the market under the trade names Eucarol ® AGE EC, Eucarol ® AGE SS,
  • the aqueous liquid detergent compositions of the invention may contain from 0.1 to 50 wt%, preferably from 10 to 30 wt%, of one or more anionic surfactants having general formula different from (I), in amount not exceeding the amount of the surfactants having general formula (I).
  • anionic surfactants having general formula different from (I) are chosen among linear or branched C 9 -Ci 5 alkylsulfate, linear or branched C 9- Ci 5 alkylbenzenesulfonates, C 8 -C 24 polyethoxylated alkyl ether sulfates containing from 1 to 20 ethoxylic groups.
  • the aqueous liquid detergent compositions of the invention may further contain non-ionic surfactants, such as: C 8- Ci 8 ethoxylated and/or propoxylated fatty alcohols containing from 1 to 20 ethoxyl or propoxyl groups and Ca-C-ie ethoxylated and/or propoxylated alkylphenols containing from 1 to 20 ethoxyl or propoxyl groups.
  • non-ionic surfactants such as: C 8- Ci 8 ethoxylated and/or propoxylated fatty alcohols containing from 1 to 20 ethoxyl or propoxyl groups and Ca-C-ie ethoxylated and/or propoxylated alkylphenols containing from 1 to 20 ethoxyl or propoxyl groups.
  • aqueous liquid detergent compositions of the invention may further contain cationic and amphoteric surfactants.
  • R is an aliphatic group, saturated or unsaturated, linear or branched, having from 6 to 20 atoms of carbon, preferably from 8 to 16 atoms of carbon;
  • G is a residue of a reducing saccharide, preferably of glucose, connected to R-O by means of an ethereal O-glycosidic bond;
  • O is an oxygen atom
  • D is an acyl residue of sulfosuccinic acid or of a carboxylic acid selected from the group consisting of citric, tartaric, maleic and malic acid, connected to an oxygen atom of G;
  • n is a number between 1 and m-1 , where m is the number of carboxylic groups in the acid that originates D;
  • x is a number from 1 to 10, representing the average degree of oligomerization of G;
  • y is a number from 1 to 10 representing the degree of average esterification of (G) x
  • [0038] are mixed with from 10 to 95 wt%, preferably from 20 to 70 wt%, of water, under stirring;
  • step A from 0.1 to 50 wt%, preferably from 10 to 30 wt%, of one or more anionic surfactants having general formula different from (I) are added while stirring to the obtained mixture, said anionic surfactants being added in an amount not exceeding the amount of the surfactant having general formula (I); preferably the anionic surfactants having general formula different from (I) are chosen among linear or branched C 9 -Ci 5 alkylsulfate, linear or branched Cg-Cisalkylbenzenesulfonates, C 8 -C24 polyethoxylated alkyl ether sulfates containing from 1 to 20 ethoxylic groups.
  • the enzymes useful for the realisation of the invention are the enzymes commercially available and normally used in detergent compositions.
  • proteases are the preferred ones, and alkaline proteases are the most preferred ones.
  • aqueous liquid detergent compositions of the invention may be contained in the aqueous liquid detergent compositions of the invention; by way of example we cite: optical brighteners, softeners, anti- foams, foaming agents, perfumes, dyes, stabilisers, suspending agents, biocides, pH regulators, sequestering agents.
  • optical brighteners, softeners, anti- foams, foaming agents, perfumes, dyes, stabilisers, suspending agents, biocides, pH regulators, sequestering agents may be contained in the aqueous liquid detergent compositions of the invention; by way of example we cite: optical brighteners, softeners, anti- foams, foaming agents, perfumes, dyes, stabilisers, suspending agents, biocides, pH regulators, sequestering agents.
  • the aqueous liquid detergent compositions of the invention may be used in household cleaning (on various surfaces, stoves, floors, glasses, sanitary wares) and for the washing of laundry, but they can also be used as heavy du
  • A is the reflectance after washing
  • B the reflectance before washing
  • C the reference reflectance value of the unstained, white swatch
  • the evaluation of the protease activity is based on the following principle: the protease hydrolyses azocasein in 20 minutes at 40°C, when the protease is dosed at 1 wt% in an aqueous mixture at pH 8 (0.1 M
  • the portion of azocasein which has not been hydrolysed is precipitated with trichloroacetic acid, while the hydrolysed azocasein is determined by spectrophotometry in the visible light spectrum.
  • the protease activity is defined as mg of azocasein hydrolysed per minute and gram of enzymatic preparation.
  • the initial protease activity (PAj) is the protease activity measured immediately after the preparation of the composition containing the protease.
  • %RPA ( APt/APj)x100
  • APt is the protease activity of the composition at the time %RPA is measured.
  • Example 1 Test of enzymatic stability of aqueous detergent compositions of the invention.
  • Aqueous based liquid detergent compositions are prepared which contain
  • Purafect ® 4000 L alkaline protease from B subtilis OGM by
  • compositions are evaluated by measuring the %RPAone hour after their preparation, using the method above described; from the time of their preparation to the time when the PAt is measured the compositions are maintained at 3O 0 C.
  • Aqueous based detergent compositions are prepared containing 0.15 %v of Savinase ® 16L (alkaline protease from B. subtilis OGM by
  • Aqueous based detergent compositions are prepared containing 0.4 %v of Purafect ® OX 4000L (alkaline protease from B subtilis OGM by Genencor, US) and variable amounts of anionic ester of alkylpolyglycosides (see the first column of Table 3)
  • compositions are evaluated by measuring the %RPA one hour after their preparation, using the method above described; from the time of their preparation to the time when the PAt is measured the compositions are maintained at 3O 0 C.
  • Aqueous detergent compositions from 1 to 17 are prepared as follows. [00110] 25 g of surfactants) (see Table 4, where the amount of a.s. of surfactant in grams in each composition is reported) are diluted with 69.5 g of demineralised water, under stirring. [00111] In sequence, under stirring, 0.5 g of protease (Purafect ® 4000 L) and 5 g of monopropylene glycol are added. [00112] The mixture is stirred for 15 minutes and the pH is regulated at 7.4-7.6 with citric acid or triethanoleamine. [00113] The washing performance is determined by measuring the average percentage of stain removed, using the above described method.
  • compositions 1-17 The average percentage of stain removed (%SR) is reported in Table 4 for each composition.
  • %SR The enzymatic stability of Compositions 1-17 is evaluated by measuring the %RPA one hour after their preparation, using the method above described; from the time of their preparation to the time when the PAt is measured the compositions are maintained at 40 0 C.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention a trait à des compositions détergentes liquides aqueuses comprenant des esters anioniques d'alkylpolyglycosides et des enzymes, et à un procédé de préparation de celles-ci ; ces compositions présentent une stabilité enzymatique à long terme et d'excellentes performances de lavage.
PCT/EP2004/050966 2003-06-13 2004-06-01 Compositions detergentes liquides aqueuses comprenant des esters anioniques d'alkylpolyglycosides et des enzymes Ceased WO2004111170A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CA002525211A CA2525211A1 (fr) 2003-06-13 2004-06-01 Compositions detergentes liquides aqueuses comprenant des esters anioniques d'alkylpolyglycosides et des enzymes
US10/560,145 US20070032395A1 (en) 2003-06-13 2004-06-01 Aqueous liquid detergent compositions comprising anionic esters of alkylpolyglycosides and enzymes
EP04741682A EP1633841A1 (fr) 2003-06-13 2004-06-01 Compositions detergentes liquides aqueuses comprenant des esters anioniques d'alkylpolyglycosides et des enzymes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT000019A ITVA20030019A1 (it) 2003-06-13 2003-06-13 Detergenti liquidi acquosi a base di esteri anionici di alchilpoliglicosidi.
ITVA2003A000019 2003-06-13

Publications (1)

Publication Number Publication Date
WO2004111170A1 true WO2004111170A1 (fr) 2004-12-23

Family

ID=33548901

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2004/050966 Ceased WO2004111170A1 (fr) 2003-06-13 2004-06-01 Compositions detergentes liquides aqueuses comprenant des esters anioniques d'alkylpolyglycosides et des enzymes

Country Status (5)

Country Link
US (1) US20070032395A1 (fr)
EP (1) EP1633841A1 (fr)
CA (1) CA2525211A1 (fr)
IT (1) ITVA20030019A1 (fr)
WO (1) WO2004111170A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2448405B2 (fr) † 2009-07-01 2017-10-18 Lamberti SpA Concentré herbicide aqueux

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110312866A1 (en) 2010-06-21 2011-12-22 Ecolab Usa Inc. Alkyl polypentosides and alkyl polyglucosides (c8-c11) used for enhanced food soil removal
US8329633B2 (en) 2010-09-22 2012-12-11 Ecolab Usa Inc. Poly quaternary functionalized alkyl polyglucosides for enhanced food soil removal
US20120046215A1 (en) 2010-08-23 2012-02-23 Ecolab Usa Inc. Poly sulfonate functionalized alkyl polyglucosides for enhanced food soil removal
US8658584B2 (en) 2010-06-21 2014-02-25 Ecolab Usa Inc. Sulfosuccinate functionalized alkyl polyglucosides for enhanced food and oily soil removal
US20110312867A1 (en) 2010-06-21 2011-12-22 Ecolab Usa Inc. Betaine functionalized alkyl polyglucosides for enhanced food soil removal
US20120046208A1 (en) 2010-08-23 2012-02-23 Ecolab Usa Inc. Poly phosphate functionalized alkyl polyglucosides for enhanced food soil removal
US8389457B2 (en) 2010-09-22 2013-03-05 Ecolab Usa Inc. Quaternary functionalized alkyl polyglucosides for enhanced food soil removal
WO2011161604A2 (fr) * 2010-06-21 2011-12-29 Ecolab Usa Inc. Polygllucosides d'alkyle fonctionnalisés pour élimination améliorée de salissures huileuses et d'aliments
US8877703B2 (en) 2010-09-22 2014-11-04 Ecolab Usa Inc. Stearyl and lauryl dimoniumhydroxy alkyl polyglucosides for enhanced food soil removal
EP2607469A1 (fr) 2011-12-20 2013-06-26 Unilever PLC Détergent liquide avec protéase et lipase
US20150252310A1 (en) 2014-03-07 2015-09-10 Ecolab Usa Inc. Alkyl amides for enhanced food soil removal and asphalt dissolution

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986005187A1 (fr) * 1985-03-07 1986-09-12 A.E. Staley Manufacturing Company Composition detergente contenant un enzyme et un agent tensio-actif glucoside
EP0554943A2 (fr) * 1992-02-03 1993-08-11 Unilever N.V. Composition détergente
US6121225A (en) * 1998-12-21 2000-09-19 Condea Vista Company Stable aqueous enzyme compositions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986005187A1 (fr) * 1985-03-07 1986-09-12 A.E. Staley Manufacturing Company Composition detergente contenant un enzyme et un agent tensio-actif glucoside
EP0554943A2 (fr) * 1992-02-03 1993-08-11 Unilever N.V. Composition détergente
US6121225A (en) * 1998-12-21 2000-09-19 Condea Vista Company Stable aqueous enzyme compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
VERZOTTI T ET AL: "ESTERICI ALCHILPOLIGLUCOSIDI (EUCAROL APG ESTERI). PER REALIZZARE DETERGENTI COSMETICI NATURALI, FUNZIONALI, DELICATI ED ECOLOGICI", COSMETIC NEWS, MILAN, IT, vol. 108, 5 June 1996 (1996-06-05), pages 183 - 186, XP000939060, ISSN: 1125-6222 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2448405B2 (fr) † 2009-07-01 2017-10-18 Lamberti SpA Concentré herbicide aqueux

Also Published As

Publication number Publication date
ITVA20030019A1 (it) 2004-12-14
EP1633841A1 (fr) 2006-03-15
CA2525211A1 (fr) 2004-12-23
US20070032395A1 (en) 2007-02-08

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